Epoxy resins from hydroxy benzamides

Abstract

New epoxy resins are prepared by reacting a hydroxybenzamide or derivative thereof with an epihalohydrin followed by dehydrohalogenation. These epoxy resins have crystalline melting points, self-cure at elevated temperatures and cure rapidly in the presence of the usual epoxy resin curing agents. Also disclosed are hydrolyzed products of these epoxy resins and subsequent reactions with polyisocyanates.

We claim: 
     
       1. A product resulting from reacting (1) a composition containing a vicinal dihydroxy-containing material or mixture of such materials represented by any one of the following formulas VIII, IX or X ##STR3## wherein each R is a divalent hydrocarbyl group having from 1 to about 18 carbon atoms, a group represented by the following formulas IV, V, VI or VII ##STR4## or R can be combined with R 5  so as to form a stable heterocyclic ring with the nitrogen atoms; each A is independently a divalent hydrocarbyl group having from 1 to about 10 carbon atoms, --O--, --S--, --S--S--, ##STR5## each R 2  and R 3  is independently hydrogen or an alkyl group having from 1 to about 4 carbon atoms; each R 4  is independently hydrogen, a hydrocarbyl or a halogen substituted hydrocarbyl group having from 1 to about 8 carbon atoms; each R 5  is independently hydrogen, a 2-hydroxy-3-halopropyl group, a 2-alkyl-2-hydroxy-3-halopropyl group, a monovalent hydrocarbyl group or a hydroxyl substituted monovalent hydrocarbyl group, said hydrocarbyl groups having from 1 to about 9 carbon atoms, said alkyl group having from 1 to about 4 carbon atoms; each R 8  is independently selected from the group represented by the following formula XV ##STR6## or the groups represented by R 5 , except that R 8  cannot be hydrogen; each R 9  is a divalent hydrocarbyl group having from 2 to about 4 carbon atoms; each X is independently hydrogen, chlorine, bromine or a hydrocarbyl or hydrocarbyloxy group having from 1 to about 9 carbon atoms; each X' is a hydroxyl group; each m independently has a value of zero or 1; n has an average value of from about 0.01 to about 6; p has an average value of from 1 to about 10; q has an average value of at least 1 and each y and z independently has a value of 1 or 2 with (2) a vicinal monoepoxy-containing material. 
     
     
       2. A product of claim 1 wherein in said vicinal dihydroxyl-containing material each R is independently a divalent hydrocarbyl group having from 2 to about 12 carbon atoms or two such groups each having from 2 to about 4 carbon atoms; A is a divalent hydrocarbyl group having from 1 to about 4 carbon atoms, each R 2 , R 3 , R 5  and X is hydrogen; R 4  is hydrogen or an alkyl group having from 1 to about 2 carbon atoms; R 9  is a divalent hydrocarbyl group having 2 carbon atoms; and m has a value of 1. 
     
     
       3. A product of claim 1 and 2 wherein said vicinal epoxy-containing material is ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide or a mixture thereof.